January: With all of the kids back in school, and cold/wet weather in most of the country, this is the perfect time to enjoy some sunshine and beaches, and head to Orlando or San Diego. Since lines at theme parks tend to be at their shortest, the weather is much better than most places in the country, you can enjoy the outdoors. Additionally, being that it’s post-holiday season, airfare tends to be at its lowest.
February: Romance is in the air in February, and there are many cities in the South that are small enough to be charming, but large enough to have amenities. The slow pace, classic southern charm, and delicious, comforting food can be an intoxicating mix. Try Savannah, Georgia, or Charleston, North Carolina. For an even more removed remote southern trip, try staying in a plantation in the Mississippi Delta.
March: This is the time to avoid the Spring-Break crowd. Enjoy the warmer air and go to Lexington to get outside, drink a mint julep, and take in some Kentucky Bluegrass music, or head to Nashville, Tennessee for some cold fruit tea, hot chicken, and even hotter country music. Or head to Washington D.C. to take in some monuments and museums during the Cherry Blossom Festival season.
April: Most people think of summer in Los Angeles as the peak for beach-going and celeb-spotting weather, but actually April is the best month for visiting sunny Southern California. You’ll experience very little rainfall, warm temperatures, and you can avoid the oppressive summer smog and heat. L.A. is the perfect place to start your summer early.
May: Spring in New York is magical. The Highline, a park built on abandoned elevated rail tracks is in bloom, Central Park is fully green, and no holidays or summer tourists will be filling the always-crowded streets. Obviously there are endless things to do in NY, but a stroll through the Village or a picnic in Central Park are wonderful ways to enjoy the city in the spring.
June: As summer and outdoor festivals and concerts start to kick into gear, check out a new city that might be off the beaten path for you. Portland, Chicago, and Philadelphia are all the top of the list for civic-minded, walkable cities in the U.S. that throw lots of summer parties, festivals, and host outdoor music concerts.
July: If ever there were a time to go to New Jersey, it’s to go “down the shore” in the summer with the crowds. Sunbathing, boardwalks, parties, and family-friendly summer fun fill the suntan lotion-scented air. Or if you feel like a quieter, more urbane summer, go to Boston. Walk the Commons, explore Cambridge and the beautiful Harvard campus, take in a game at Wrigley field, stay near the water for Harborfest and cooler temps, and shop in Back Bay.
August: One of the warmest months that San Francisco can boast (a lot of the spring and summer are surprisingly cold and damp) with lots of outdoor activities, the best burrito around, ethnic neighborhoods, parks, Fisherman’s Wharf, cable cars, and some great arts and theater, San Francisco is the perfect way to spend a summer weekend. (Then again, Mark Twain quipped that the coldest winter he ever spent was summer in San Francisco)
September: Enjoy fall foliage, spiced drinks, and the ever-crispier air in a traditional place, a la Vermont or New England, but don’t forget Seattle, which also boasts beautiful fall colors and temperatures. Lots of autumnal spirit, hay bales, and apple picking are to be had all over the country.
October: Head to Nantucket for Fall Restaurant Week and the Nantucket Arts Festival, Cranberry harvests, and great craft beer. Enjoy the seaside town off-season with brisk sailing and romantic beaches.
November: Santa Fe is full of fall festivals and the arts and crafts movement is represented from top to bottom. With a winter Indian Market, a sprawling Artist’s Market, and temperatures in November that range from 70’s at the start of the month to 50’s by Thanksgiving, it’s a comfortable time to spend in the Southwest. Start your holiday shopping with independent craftspeople, and avoid the chill that may be creeping in back home.
December: Bundle up and get cozy by a fire, and enjoy the start of winter by skiing, snowboarding, or just hiking in the brisk mountain air. Keystone in Colorado, Mammoth Mountain in California, Alta in Utah, and Sunday River in Maine are all resorts that start the snow season early enough to enjoy in December, even if there isn’t snow on the ground where you live.